Acetone → HCID 67191351, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of 2(R)-(3-chloro-4-methylsulfanyl-phenyl)-3-(3-oxo-cyclobutyl)-propionic acid (0.56 g, 1.88 mmol) dissolved in acetone (15 ml) and cooled to 0° C. in an ice bath was added potassium peroxymonosulfate (Oxone R, 2.3 g, 3.76 mmol) in water (6 ml). The ice bath was removed and the reaction stirred at 25° C. for 20 min. After such a time, it was filtered and washed with acetone and then concentrated in vacuo to remove acetone. The residue was dissolved in ethyl acetate, washed with water and then saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting reaction was dissolved in methanol and cooled to 0° C. in an ice bath. To this was slowly added potassium permanganate (0.32 g, 2.02 mmol) dissolved in water (8 ml). The reaction was then allowed to warm to 25° C. and stirred for 3 h. After this time it was filtered through short celite pad, washed with methanol and evaporated in vacuo. Purification on an AnaLogix Intelliflash system (40 g column, 3% methanol/methylene chloride+1% acetic acid) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclobutyl)-propionic acid (0.13 g, 21%) as a white foam: 1H NMR (300 MHz, CDCl3) δ ppm 2.07-2.18 (m, 1H, CH of CH2), 2.26-2.50 (m, 2H, CH and CH of CH2), 2.64-2.85 (m, 2H, 2×CH or 2×CH2), 3.09-3.24 (m, 2H, 2×CH or 2×CH2), 3.28 (s, 3H, SO2CH3), 3.65 (t, J=7.4 Hz, 1H, ArCHCO2), 7.44 (dd, Jm=1.6 Hz, Jo=8.2 Hz, 1H, Ar), 7.55 (d, Jm=1.6 Hz, 1H, Ar), 8.15 (d, Jo=8.2 Hz, 1 H, Ar).

Provenance & Evidence